Formic Acid → 4-(2-Carbamoyl-2,2-diphenylethyl)piperidine

HRID 974970Notes

Reaction equation

HRID 974970 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([C:28](=[O:30])[NH2:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)=O>[Pd].CO>[C:28]([C:15]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)(=[O:30])[NH2:29]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 19970196HCID 19970196, compound

Product 1

HCID 199701994-(2-Carbamoyl-2,2-diphenylethyl)piperidineYield 87.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on charcoal (900 mg) was added portionwise over 10 minutes to a stirred, ice-cooled solution of 1-benzyl-4-(2-carbamoyl-2,2-diphenylethyl)piperidine (890 mg, 2.23 mmol) (see Example 17) and formic acid (1.0 ml) in methanol (19 ml) and the mixture stirred at room temperature for 24 hours, filtered and evaporated. The residue was partitioned between dichloromethane and saturated aqueous sodium carbonate solution and the organic layer was dried over magnesium sulphate and evaporated to give the title compound (600 mg, 87%) as a colourless foam which was characterised by its 1H-NMR spectrum.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was partitioned between dichloromethane and saturated aqueous sodium carbonate solution
  4. dry with materialthe organic layer was dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-09e067f1a0254d2380d9ce43565a2878
Source dataset
uspto-grants-1997_03
Patent number
US05607950

Reaction notes

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